Methyl iodide → 1-benzyl-2-(methoxycarbonyl)-5-(methylthio)-3,4-dihydro-2H-pyrrolium iodide

HRID 1394072Notes

Reaction equation

HRID 1394072 reaction equation
[CH2:1]([N:8]1[C:12](=[S:13])[CH2:11][CH2:10][CH:9]1[C:14]([O:16][CH3:17])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I:18][CH3:19]>>[I-:18].[CH2:1]([N+:8]1[CH:9]([C:14]([O:16][CH3:17])=[O:15])[CH2:10][CH2:11][C:12]=1[S:13][CH3:19])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 6328Methyl iodideHCID 14759675Methyl 1-benzyl-5-thioxo-2-pyrrolidinecarboxylate

Product 1

HCID 865958731-benzyl-2-(methoxycarbonyl)-5-(methylthio)-3,4-dihydro-2H-pyrrolium iodide

Procedure

Methyl 1-benzyl-5-thioxo-2-pyrrolidinecarboxylate (16.5 g, 66.2 mmol) in iodomethane (70 mL) was stirred overnight at room temperature. The mixture was concentrated under reduced pressure to provide the title compound which was used in the next step without further purification. 1H NMR (CDCl3) δ 2.24 (m, 1H), 3.04 (s, 3H), 3.16 (m, 1H), 3.25 (m, 1H), 3.63 (s, 3H), 4.29 (dd, 1H), 4.72 (d, 1H), 4.89 (dd, 1H), 5.14 (d, 1H), 7.43 (m, 3H), 7.51 (m, 2H).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-6882882ee37242cd8f62d6f51d9ff46f
Source dataset
uspto-grants-2008_03
Patent number
US07348343B2

Reaction notes

Loading…